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Cheap flights from Jamaica to Illinois from $183

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Jamaica to Illinois departing on 12/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Jamaica to Illinois

Recent round-trip flight deals from Jamaica to Illinois

Enter your travel dates to find the best prices.
United Airlines Logo
4:33 pm - 9:05 am
MBJ
-
ORD
16h 32m
1 stop
United Airlines Logo
11:15 am - 3:10 pm
ORD
-
MBJ
27h 55m
1 stop
$321United Airlines
Sat, Jul 4 - Sat, Jul 11
United Airlines Logo
4:12 pm - 11:31 pm
MBJ
-
ORD
7h 19m
1 stop
United Airlines Logo
6:29 am - 3:26 pm
ORD
-
MBJ
8h 57m
1 stop
$326United Airlines
Fri, Jul 17 - Sun, Jul 19
JetBlue Logo
3:59 pm - 11:44 pm
MBJ
-
ORD
8h 45m
1 stop
JetBlue Logo
7:00 am - 2:54 pm
ORD
-
MBJ
6h 54m
1 stop
$334JetBlue
Thu, Nov 12 - Mon, Nov 16
American Airlines Logo
2:12 pm - 6:55 pm
MBJ
-
ORD
4h 43mnonstop
American Airlines Logo
9:00 am - 1:12 pm
ORD
-
MBJ
4h 12mnonstop
$379American Airlines
Thu, Aug 13 - Mon, Aug 17
American Airlines Logo
2:12 pm - 6:55 pm
MBJ
-
ORD
4h 43mnonstop
American Airlines Logo
6:45 am - 2:23 pm
ORD
-
MBJ
7h 38m
1 stop
$384American Airlines
Thu, Aug 13 - Mon, Aug 17
Frontier Logo
1:26 pm - 10:11 pm
MBJ
-
MDW
8h 45m
1 stop
Frontier Logo
6:00 am - 12:21 pm
MDW
-
MBJ
6h 21m
1 stop
$435Frontier
Sat, Jul 4 - Tue, Sep 1
Frontier Logo
1:26 pm - 10:11 pm
MBJ
-
MDW
8h 45m
1 stop
Frontier Logo
6:05 am - 12:27 pm
MDW
-
MBJ
6h 22m
1 stop
$455Frontier
Sat, Jul 4 - Sat, Jul 11
JetBlue Logo
6:00 am - 1:39 pm
KIN
-
ORD
7h 39m
1 stop
JetBlue Logo
6:27 pm - 8:14 pm
ORD
-
KIN
25h 47m
1 stop
$460JetBlue
Tue, Sep 1 - Tue, Sep 1
Southwest Logo
2:30 pm - 6:35 pm
MBJ
-
MDW
4h 05mnonstop
Southwest Logo
6:30 am - 12:55 pm
MDW
-
MBJ
6h 25m
1 stop
$474Southwest
Sat, Jul 4 - Tue, Sep 1
Southwest Logo
2:30 pm - 6:35 pm
MBJ
-
MDW
4h 05mnonstop
Southwest Logo
6:30 am - 12:55 pm
MDW
-
MBJ
6h 25m
1 stop
$544Southwest
Sat, Jul 4 - Tue, Sep 1

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United Airlines flights from Jamaica to Illinois

Our best United Airlines deals on Jamaica to Illinois flight tickets
United Airlines
Jul 4
MBJ4:33 pmMontego Bay Sangster Intl
16h 32m
1 stop
ORD9:05 amChicago O'Hare Intl
Jul 11
ORD11:15 amChicago O'Hare Intl
27h 55m
1 stop
MBJ3:10 pmMontego Bay Sangster Intl
$321
United Airlines
Jul 17
MBJ4:12 pmMontego Bay Sangster Intl
7h 19m
1 stop
ORD11:31 pmChicago O'Hare Intl
Jul 19
ORD6:29 amChicago O'Hare Intl
8h 57m
1 stop
MBJ3:26 pmMontego Bay Sangster Intl
$326
United Airlines
Aug 13
MBJ4:12 pmMontego Bay Sangster Intl
7h 28m
1 stop
ORD11:40 pmChicago O'Hare Intl
Aug 17
ORD8:45 amChicago O'Hare Intl
6h 25m
1 stop
MBJ3:10 pmMontego Bay Sangster Intl
$347

Air Canada flights from Jamaica to Illinois

Our best Air Canada deals on Jamaica to Illinois flight tickets
Air Canada
Jun 24
MBJ12:30 pmMontego Bay Sangster Intl
19h 15m
2 stops
ORD7:45 amChicago O'Hare Intl
Jun 30
ORD8:40 pmChicago O'Hare Intl
14h 40m
1 stop
MBJ11:20 amMontego Bay Sangster Intl
$493
Air Canada
Jun 24
MBJ12:30 pmMontego Bay Sangster Intl
19h 15m
2 stops
ORD7:45 amChicago O'Hare Intl
Jul 25
ORD3:40 pmChicago O'Hare Intl
19h 40m
2 stops
MBJ11:20 amMontego Bay Sangster Intl
$497
Air Canada
Jun 24
MBJ12:30 pmMontego Bay Sangster Intl
19h 15m
2 stops
ORD7:45 amChicago O'Hare Intl
Jun 30
ORD8:40 pmChicago O'Hare Intl
14h 40m
1 stop
MBJ11:20 amMontego Bay Sangster Intl
$525

momondo Fare Finder

 
Customize your flight search to find flights from Jamaica to Illinois that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated June 12, 2026.
Use the filters below to find and compare flights from Jamaica to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 7/4

4:33 pm-9:05 am

1 stop16h 32m

Chicago O'Hare Intl

Sat 7/11

11:15 am-3:10 pm

1 stop27h 55m

$321

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 7/17

4:12 pm-11:31 pm

1 stop7h 19m

Chicago O'Hare Intl

Sun 7/19

6:29 am-3:26 pm

1 stop8h 57m

$326

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 11/12

3:59 pm-11:44 pm

1 stop8h 45m

Chicago O'Hare Intl

Mon 11/16

7:00 am-2:54 pm

1 stop6h 54m

$334
Quickest round-trip

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 8/13

2:12 pm-6:55 pm

Nonstop4h 43m

Chicago O'Hare Intl

Mon 8/17

9:00 am-1:12 pm

Nonstop4h 12m

$379

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 8/13

2:12 pm-6:55 pm

Nonstop4h 43m

Chicago O'Hare Intl

Mon 8/17

6:45 am-2:23 pm

1 stop7h 38m

$384

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 7/4

1:26 pm-10:11 pm

1 stop8h 45m

Chicago Midway

Tue 9/1

6:00 am-12:21 pm

1 stop6h 21m

$435

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 7/4

1:26 pm-10:11 pm

1 stop8h 45m

Chicago Midway

Sat 7/11

6:05 am-12:27 pm

1 stop6h 22m

$455

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 9/1

6:00 am-1:39 pm

1 stop7h 39m

Chicago O'Hare Intl

Tue 9/1

6:27 pm-8:14 pm

1 stop25h 47m

$460

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 7/4

2:30 pm-6:35 pm

Nonstop4h 05m

Chicago Midway

Tue 9/1

6:30 am-12:55 pm

1 stop6h 25m

$474

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 7/4

2:30 pm-6:35 pm

Nonstop4h 05m

Chicago Midway

Tue 9/1

6:30 am-12:55 pm

1 stop6h 25m

$544

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Illinois from

How to get the cheapest flight ticket from Jamaica to Illinois

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Illinois?

The cheapest month to fly to Illinois from Jamaica is in April. Flight prices, which tend to average around $146, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of April, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $204.

What is the cheapest day to depart on your flight to Illinois?

The cheapest day to depart from Jamaica to Illinois is on a Thursday when prices can be found for as low as $395. Flights from Jamaica to Illinois on a Monday will generally be more expensive and average around $543. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Illinois?

Our most recent data shows that the best time of day to fly to Illinois is in the afternoon. Flights from Jamaica to Illinois during this time can be as low as $454. Flights at noon are often more expensive with an average ticket price of $457.

What is the cheapest Jamaica to Illinois flight route?

Fly from Montego Bay Sangster Intl to Chicago O'Hare Intl for the best Jamaica - Illinois flight prices

What cabin class options are available on Jamaica to Illinois flights?

There are 3 cabin classes available to choose from on Jamaica to Illinois flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Jamaica to Illinois flights?

You could potentially save up to 5% on your flight if you consider stops on a Jamaica to Illinois flight.

Cheap Jamaica to Illinois flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Jamaica to Illinois

Best Price Found

$289

Fastest flight time

4h 39m

Direct flights

Every day

Airports in Illinois

98 airports
The best one-way flight to Illinois from Jamaica in the past 72 hours is $289. The best round-trip flight deal from Jamaica to Illinois found on momondo in the last 72 hours is $422.
The fastest flight from Jamaica to Illinois takes 4h 39m
Direct flights go from Jamaica to Illinois every day.
There are 98 airports in Illinois. From Jamaica there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

Frequently asked questions about flying from Jamaica to Illinois

  • When did momondo last update prices for flights from Jamaica to Illinois?

    Prices for flights from Jamaica to Illinois were last updated today.

  • How many operators does momondo search for flights from Jamaica to Illinois?

  • How old do you have to be to fly from Jamaica to Illinois?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Jamaica to Illinois.

  • What documentation or ID do you need to fly to Illinois?

    The travel and health documents you'll need for your trip to Illinois may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Illinois. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Jamaica to Illinois?

Best airlines flying from Jamaica to Illinois

Compare and see reviews for airlines that fly from Jamaica to Illinois with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $280Free CancellationRating
7.4
9,810 reviews
Search United Airlines flights
American AirlinesPriceFrom $281Free CancellationRating
7.1
11,644 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Jamaica to Illinois?

It is quick and easy to find Jamaica to Illinois flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Illinois that suits you.

Can I find flights from Jamaica to Illinois with flexible booking policies on momondo?

momondo does allow users to show only those flights to Illinois from Jamaica which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Jamaica to Illinois?

momondo provides multiple filters to help you find the best flight to Illinois from Jamaica. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Jamaica to Illinois right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Jamaica to Illinois now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Illinois and let you know when they change.

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